Substituent-controlled construction of A4B2-hexaphyrins and A3B-porphyrins: a mechanistic evaluation

Seda Cinar; Dilek Isik Tasgin; Canan Unaleroglu

doi:10.3762/bjoc.19.135

Substituent-controlled construction of A₄B₂-hexaphyrins and A₃B-porphyrins: a mechanistic evaluation

Beilstein J Org Chem. 2023 Dec 6:19:1832-1840. doi: 10.3762/bjoc.19.135. eCollection 2023.

Authors

Seda Cinar^{1

2}, Dilek Isik Tasgin³, Canan Unaleroglu¹

Affiliations

¹ Department of Chemistry, Hacettepe University, Beytepe Campus 06800, Ankara, Turkey.
² Ankara Hacı Bayram Veli University, Chemistry Department, Polatli Campus, 06900 Polatli, Ankara, Turkey.
³ Inter-Curricular Courses Department, Çankaya University, Central Campus, 06790 Etimesgut, Ankara, Turkey.

Abstract

A substituent-dependent construction of novel A₃B-porphyrins along with A₄B₂-hexaphyrins was realized by the reactions of N-tosylimines and meso-aryl-substituted tripyrranes in the presence of Cu(OTf)₂ as the catalyst. The reaction mechanism of the presented method was studied on model reactions by electrospray-ionization time-of-flight (HRESI-TOF) mass spectral analysis in a timely manner. The analytical results indicated that the observed azafulvene-ended di- and tripyrrolic intermediates are responsible for the formation of porphyrinogen and hexaphyrinogen forms.

Keywords: A3B-porphyrin; A4B2-hexaphyrin; Cu(OTf)2 catalysis; HRESI–TOF analysis; N-tosylimine.

Grants and funding

SC thanks The Scientific and Technological Research Council of Turkey (TUBITAK) for doctoral scholarship (2211-C Domestic Ph.D. Scholarship Programme for Priority Areas).